Please do not adjust margins
RSC Advances
Page 4 of 5
COMMUNICATION
Journal Name
Li, Z.-T. Wang, L. Zhu, X.-Q. Tan and C.-Z. Li, J. Am. Chem. Soc.,
In conclusion, we have described the first example of a
selectfluor-mediated intermolecular C–O cross coupling
reaction of simple aldehydes with NHPI and NHSI without
using any metal catalyst. The resulting products can be directly
converted into amides in one pot. Various aldehydes including
aliphatic aldehydes such as propionaldehyde, butyraldehyde,
and pentanal were efficient, which made this CDC reaction
very attractive. Further investigations to gain a detailed
mechanistic understanding of this reaction and apply this
strategy in other oxidative coupling reactions are underway in
our lab.
We gratefully acknowledge the Science & Technology
Foundation of Henan Province, the Foundation of Henan
Educational Committee (15A150029), Jilin Province Key
Laboratory of Organic Functional Molecular Design & Synthesis
(130028651), Henan province key laboratory of new opto-
electronic functional materials and AYNU-KP-A04 for financial
support.
2014, 136, 16439; (j) C. W. Kee, K. F. Chin, M. W. Wong and
C.-H. Tan, Chem. Commun., 2014, 50, 8D2O1I1:.10.1039/C6RA22653A
(a) S. Bloom, C. R. Pitts, D. C. Miller, N. Haselton, M. G. Holl, E.
7
8
Urheim and T. Lectka, Angew. Chem., Int. Ed., 2012, 51
,
10580; (b) Y. Amaoka, M. Nagatomo and M. Inoue, Org. Lett.,
2013, 15, 2160.
For recent reviews, see: (a) S. Stavber and M. Zupan, Acta
Chim. Slov., 2005, 52, 13; (b) K. M. Engle, T.-S. Mei, X.-S.
Wang and J.-Q. Yu, Angew. Chem., Int. Ed., 2011, 50, 1478;
Recent progress for selectfluor-mediated oxidation, see: (c)
J.-D. Zhou, C. Jin, X.-H. Li and W.-K. Su, RSC Adv., 2015, 5,
7232; (d) C. A. Dannenberg, V. Bizet, L.-H. Zou and C. Bolm,
Eur. J. Org. Chem., 2015, 2015, 77; (e) N. Ahlsten and B.
Martín-Matute, Chem. Commun., 2011, 47, 8331; (f) M. H.
Daniels and T. Hubbs, Tetrahedron Lett., 2011, 52, 3543; (g)
M. Kirihara, S. Naito, Y. Ishizuka, H. Hanai and T. Noguchi,
Tetrahedron Lett., 2011, 52, 3086; (h) Z. Jin, B. Xu and G. B.
Hammond, Tetrahedron Lett., 2011, 52, 1956; (i) T. C.
Allmann, R.-P. Moldovan, P. G. Jones and T. Lindel, Chem.-
Eur. J., 2016, 22, 111; (j) R. Guo, Z.-J. Zhang, F. Shi and P.-P.
Tang, Org. Lett., 2016, 18, 1008; (k) Y.-K. Liu, J. Zhu, J.-Q.
Qian and Z.-Y. Xu, J. Org. Chem., 2012, 77, 5411; (l) T. de
Haro and C. Nevado, Chem. Commun., 2011, 47, 248; (m) Y.
Lin, L. Zhu, Y. Lan and Y. Rao, Chem.-Eur. J., 2015, 21, 14937.
(a) Y.-H. Lv, X. Wang, H. Cui, K. Sun, W.-Y. Pu, G. Li, Y.-T. Wu,
Notes and references
9
1
(a) G. H. L. Nefkens and G. I. Tesser, J. Am. Chem. Soc., 1961,
83, 1263; (b) G. W. Anderson, J. E. Zimmerman and F. M.
Callahan, J. Am. Chem. Soc., 1964, 86, 1839; (c) G. W. Cline
and S. B. Hanna, J. Am. Chem. Soc., 1987, 109, 3087; (d) M.
Bodanzsky, Principles of Peptide Synthesis 2nd ed., Springer,
New York, 1993.
J.-L. He and X.-R. Ren, RSC Adv., 2016, 6, 74917; (b) Y.-H. Lv,
Y.-Y. Zheng, Y. Li, T. Xiong, J.-P. Zhang, Q. Liu and Q. Zhang,
Chem. Commun., 2013, 49, 8866; (c) Y.-H. Lv, Y. Li, T. Xiong, Y.
Lu, Q. Liu and Q. Zhang, Chem. Commun., 2014, 50, 2367; (d)
Y.-H. Lv, K. Sun, T.-T. Wang, Y.-T. Wu, G. Li, W.-Y. Pu and S.-K.
Mao, Asian J. Org. Chem., 2016,
T.-T. Wang, G. Li, W.-Y. Pu, N.-N, Chai, H.-H. Shen and Y.-T.
Wu, RSC Adv., 2015, , 72142.
5, 325; (e) Y.-H. Lv, K. Sun,
2
(a) W. Van Brussel and C. F. Van Sumere, Bull. SOC. Chim.
Belg., 1978, 87, 791; (b) B. Schmidt, I. Franke, F. J. Witteler
and M. Binder, Helu. Chim. Acta, 1983, 66, 2564; (c) J. M.
Stadel, D. B. P. Goodman, R. E. Galarday and H. Rasmussen,
Biochemistry, 1978, 17, 1403; (d) B. Manz, A. Heubner, I.
5
10 (a) T. Qin, J. Cornella, C. Li, L. R. Malins, J. T. Edwards, S.
Kawamura, B. D. Maxwell, M. D. Eastgate and P. S. Baran,
Science, 2016, 352, 801; (b) K. M. M. Huihui, J. A. Caputo, Z.
Melchor, A. M. Olivares, A. M. Spiewak, K. A. Johnson, T. A.
DiBenedetto, S. Kim, L. K. G. Ackerman and D. J. Weix, J. Am.
Chem. Soc., 2016, 138, 5016; (c) G. Wang, Q.-Y. Yu, J. Wang, S.
Kohler, H.-J. Grill and K. Pollow, Eur. J. Biochem., 1983, 131
,
333; (e) R. H. Raja, R. D. LeBoeuf, G. W. Stone and P. H.
Weigel, Anal. Biochem., 1984, 139, 168.
3
4
(a) E. Grochowski and J. Jurczak, Synthesis, 1977, 277; (b) H.
Ogura, T. Kobayashi, K. Shimizu, K. Kawabe and K. Takeda,
Tetrahedron Lett., 1979, 20, 4745; (c) S. Kim and K. Y. Ko, J.
Chem. Soc. Chem. Commun., 1985, 473; (d) P. Pöchlauer and
W. Hendel, Tetrahedron, 1998, 54, 3489; (e) M. Kim and K. J.
Han, Synth. Commun., 2009, 39, 4467.
Wang, S.-Y. Chen and X.-Q. Yu, RSC Adv., 2013, 3, 21306; (d)
M. J. Schnermann and L. E. Overman, Angew. Chem., Int. Ed.,
2012, 51, 9576; (e) G. Pratsch, G. L. Lackner and L. E.
Overman, J. Org. Chem., 2015, 80, 6025.
11 (a) Y.-Y. Liu, J. Yang, R.-J. Song and J.-H. Li, Adv. Synth. Catal.,
2014, 356, 2913; (b) D. Shi, H.-T. Qin, C. Zhu and F. Liu, Eur. J.
Org. Chem., 2015, 2015, 5084.
(a) I. B. Krylov, V. A. Vil’ and A. O. Terent’ev, Beilstein J. Org.
Chem., 2015, 11, 92; (b) H. Yao, Y. Tang and K. Yamamoto,
Tetrahedron Lett., 2012, 53, 5094; (c) A. Schulze and A.
Giannis, Adv. Synth. Catal., 2004, 346, 252; (d) N.-W. Wang,
R.-H. Liu, Q. Xu and X.-M. Liang, Chem. Lett., 2006, 35, 566.
(a) B. Tan, N. Toda and C. F. Barbaras III, Angew. Chem., Int.
Ed., 2012, 51, 12538; (b) M. Dinda, C. Bose, T. Ghosh and S.
12 (a) F. Recupero and C. Punta, Chem. Rev., 2007, 107, 3800; (b)
Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama and Y.
Nishiyama, J. Org. Chem., 1996, 61, 4520; (c) Y. Ishii, K.
Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama and Y.
Nishiyama, J. Org. Chem., 1995, 60, 3934; (d) B. Saha, N.
Koshino and J. H. Espenson, J. Phys. Chem. A, 2004, 108, 425;
(e) C. Einhorn, J. Einhorn, C. Marcadal and J.-L. Pierre, Chem.
Commun., 1997, 447; (f) C. Annunziatini, M. F. Gerini, O.
Lanzalunga and M. Lucarini, J. Org. Chem., 2004, 69, 3431.
13 (a) C. Chatgilialoglu, D. Crich, M. Komatsu and I. Ryu, Chem.
Rev., 1999, 99, 1991; (b) S. Tsujimoto, S. Sakaguchi and Y.
Ishii, Tetrahedron Lett., 2003, 44, 5601; (c) G. A. DiLabio, K. U.
5
6
Maity, RSC Adv., 2015, 5, 44928.
Electrophilic fluorinating reagents, see: (a) P. T. Nyffeler, S. G.
Durón, M. D. Burkart, S. P. Vincent and C.-H. Wong, Angew.
Chem., Int. Ed., 2005, 44, 192; (b) R. E. Banks, S. N.
Mohialdin-Khaffa, G. S. Lal, I. Sharif and R. G. Syvret, J. Chem.
Soc., Chem. Commun., 1992,
Q.-F. Liua and G.-S. Zhang, Green Chem., 2012, 14, 1159; (d)
R.-Y. Lin, S.-T. Ding, Z.-Z. Shi and N. Jiao, Org. Lett., 2011, 13
8, 595; (c) J.-J. Bi, Z.-G Zhang,
Ingold, M. D. Roydhouse and J. C. Walton, Org. Lett., 2004, 6,
,
4319; (d) M. Conte, H. Miyamura, S. Kobayashi and V.
Chechik, Chem. Commun., 2010, 46, 145; (e) Z.-J. Liu, J. Zhang,
S.-L. Chen, E.-B. Shi, Y. Xu and X.-B. Wan, Angew. Chem., Int.
Ed., 2012, 51, 3231.
4498; (e) P. A. Champagne, J. Desroches, J.-D. Hamel, M.
Vandamme and J.-F. Paquin, Chem. Rev., 2015, 115, 9073;
Radical fluorinating reagents, see: (f) C.-W. Zhang, Z.-D. Li, L.
Zhu, L.-M. Yu, Z.-T. Wang and C.-Z. Li, J. Am. Chem. Soc., 2013,
135, 14082; (g) M. Rueda-Becerril, C. C. Sazepin, J. C. T.
Leung, T. Okbinoglu, P. Kennepohl, J. F. Paquin and G. M.
Sammis, J. Am. Chem. Soc., 2012, 134, 4026; (h) Z.-D. Li, L.-Y.
Song and C.-Z. Li, J. Am. Chem. Soc., 2013, 135, 4640; (i) Z.-D.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins